公开(公告)号：US20150259715A1

公开(公告)日：2015-09-17

申请号：US14431193

申请日：2014-02-18

Applicant: API CORPORATION

Inventor： Kuniki Kino ,  Ryotaro Hara ,  Ryoma Miyake ,  Hiroshi Kawabata

IPC: C12P13/08 ,  C12N9/02 ,  C12P17/12

CPC classification number: C12P13/08 ,  C12N9/0071 ,  C12P13/04 ,  C12P17/12 ,  C12Y114/11 ,  C12Y114/11004 ,  Y02P20/52

Abstract: The present invention aims to provide a method for efficiently producing hydroxy-L-lysine. The present invention provides a method for producing hydroxy-L-lysine, the method comprising allowing 2-oxoglutarate-dependent L-lysine hydroxylase, a cell containing 2-oxoglutarate-dependent L-lysine hydroxylase, a processed product of the cell, and/or a culture broth obtained by culturing the cell, to act on L-lysine to produce hydroxy-L-lysine represented by the following General Formula (I) (wherein each of R1, R2 and R3 represents a hydrogen atom or hydroxyl group, with the proviso that at least one of R1, R2 and R3 represents a hydroxyl group).

Abstract translation: 本发明的目的在于提供一种高效生产羟基-L-赖氨酸的方法。 本发明提供一种生产羟基-L-赖氨酸的方法，该方法包括使2-氧戊二酸依赖性L-赖氨酸羟化酶，含有2-氧戊二酸依赖性L-赖氨酸羟化酶的细胞，细胞的加工产物和/ 或通过培养细胞获得的培养液，作用于L-赖氨酸以产生由以下通式（I）表示的羟基-L-赖氨酸（其中R1，R2和R3各自表示氢原子或羟基，与 条件是R 1，R 2和R 3中的至少一个表示羟基）。

公开(公告)号：US20150239853A1

公开(公告)日：2015-08-27

申请号：US14424912

申请日：2013-08-30

Applicant: API CORPORATION

Inventor： Masahiko Seki

IPC: C07D257/04 ,  C07D405/14 ,  C07D403/10

CPC classification number: C07D257/04 ,  C07B37/04 ,  C07D403/10 ,  C07D405/14

Abstract: The invention provides a production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by RAxP(O)(OM)y wherein each symbol is as defined herein.

Abstract translation: 本发明提供式[3]的联芳基化合物或其盐的制备方法，包括使式[1]的2-苯基唑衍生物或其盐与式[2]的苯衍生物或 （a）一元羧酸金属盐，（b）二羧酸金属盐，（c）磺酸金属盐和（d）一种或多种金属催化剂，碱， 由RAxP（O）（OM）y表示的磷酸酯或磷酰胺金属盐，其中每个符号如本文所定义。

公开(公告)号：US20240391860A1

公开(公告)日：2024-11-28

申请号：US18681328

申请日：2022-08-26

Applicant: API CORPORATION

Inventor： Hirotsugu TANIIKE ,  Shunsuke TSUJI ,  Masaki NAGAHAMA ,  Yurie KOBA

IPC: C07C51/367 ,  C07C51/47

Abstract: Salicylic acid is produced with high productivity by reacting 2-halogenated benzoic acid in an aqueous solvent at a reaction temperature of 155° C. or higher and 300° C. or lower in the presence of a copper source and a ligand. Preferably, the method further includes a purification step A in which the obtained salicylic acid is brought into contact with a styrene-based synthetic adsorbent and/or a purification step B in which the obtained salicylic acid is brought into contact with zeolite. The compound is led to raw materials for various pharmaceuticals or intermediates thereof (for example, acetylsalicylic acid).

公开(公告)号：US20240351978A1

公开(公告)日：2024-10-24

申请号：US18738245

申请日：2024-06-10

Applicant: API CORPORATION

Inventor： Masaki NAGAHAMA ,  Hideki OOMIYA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC: C07C253/20 ,  C07C51/06 ,  C07C57/38 ,  C07C255/33

CPC classification number: C07C253/20 ,  C07C51/06 ,  C07C57/38 ,  C07C255/33 ,  C07C2602/10

Abstract: The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

公开(公告)号：US20240002340A1

公开(公告)日：2024-01-04

申请号：US18243409

申请日：2023-09-07

Applicant: API CORPORATION

Inventor： Masato MURAI ,  Jun TAKEHARA ,  Daiki OKADO

IPC: C07D211/60

CPC classification number: C07D211/60

Abstract: A method for producing a compound represented by the formula (1):




wherein LG is a leaving group, PG1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), comprising



reacting a compound represented by the formula (6):








with an amino group protecting agent to obtain a compound represented by the formula (7):




or a salt thereof;



reacting the aforementioned compound represented by the formula (7) with a lactonization agent to obtain a compound represented by the formula (8):










reacting the aforementioned compound represented by the formula (8) with an esterification agent to obtain a compound represented by the formula (9):








and



reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.

公开(公告)号：US11643386B2

公开(公告)日：2023-05-09

申请号：US17295222

申请日：2020-10-28

Applicant: API CORPORATION

Inventor： Masaki Nagahama ,  Daiki Okado ,  Hirotsugu Taniike

IPC: C07C253/22

CPC classification number: C07C253/22

Abstract: High purity 2-naphthylacetonitrile with fewer impurities can be used as a starting material or intermediate for synthesizing various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, may include: subjecting 2′-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; and reacting the 2-naphthylacetic acid obtained in the subjecting, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.

公开(公告)号：US20210024905A1

公开(公告)日：2021-01-28

申请号：US17043339

申请日：2019-03-29

Applicant: API CORPORATION

Inventor： Toyokazu YOSHIDA ,  Koichi ISHIDA ,  Ryoma MIYAKE ,  Takanobu IURA ,  Hiroshi KAWABATA

IPC: C12N9/18 ,  C12P41/00 ,  C12P7/62

Abstract: The present invention provides a novel hydrolase that can industrially produce optically highly pure (1S,2S)-1-alkoxycarbonyl-2-vinylcyclopropane carboxylic acid with high efficiency at low costs, and a production method using the hydrolase.

公开(公告)号：US20190315696A1

公开(公告)日：2019-10-17

申请号：US16442770

申请日：2019-06-17

Applicant: API CORPORATION

Inventor： Naoyuki WATANABE ,  Tomoko MAEDA ,  Yasumasa DEKISHIMA ,  Hiroshi KAWABATA ,  Masaki NAGAHAMA

IPC: C07D239/42 ,  C12N9/04 ,  C12P17/12

Abstract: An object of the present invention is to provide a novel method capable of producing rosuvastatin calcium and intermediates therefor efficiently, inexpensively and with high purity. The present invention provides a method of efficiently producing rosuvastatin calcium and intermediates therefor having a high purity at an industrial scale, without using an extremely low temperature reaction or a special asymmetric catalyst.

公开(公告)号：US20180222865A1

公开(公告)日：2018-08-09

申请号：US15749377

申请日：2016-08-05

Applicant: API CORPORATION

Inventor： Naoyuki WATANABE ,  Takanobu IURA ,  Hideki OOMIYA ,  Masaki NAGAHAMA

IPC: C07D215/14 ,  C12P17/12

Abstract: Production of pitavastatin calcium safely on an industrial scale with a high yield and high selectivity at low cost. A method of producing pitavastatin calcium including step (i) for acetalizing a compound represented by the formula (1) to give a compound represented by the formula (3), step (ii) for reacting a compound represented by the formula (3) with an acid to give a compound represented by the formula (4), and step (iii) for hydrolyzing a compound represented by the formula (4) and reacting same with a calcium compound.

公开(公告)号：US09790181B2

公开(公告)日：2017-10-17

申请号：US15108141

申请日：2014-12-26

Applicant: API CORPORATION

Inventor： Jun Takehara ,  Masato Murai ,  Takashi Ohtani ,  Tomoko Maeda ,  Tsugihiko Hidaka

IPC: C07D211/16 ,  C07D498/08 ,  C07D211/60 ,  C07C309/66 ,  C07C233/47

CPC classification number: C07D211/60 ,  C07C233/47 ,  C07C309/66 ,  C07D498/08 ,  Y02P20/55

Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).